Islesboro Vacation Packages
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Your Islesboro Vacation
When you organize a vacation package to Islesboro, you can relax and enjoy your getaway knowing your travel plans are in order. Discover the many charms of this amazing city from your base in a neighborhood like Bayside, which is great for history. If sightseeing is on the agenda during your trip to Islesboro, stop by major attractions like Windsor Chairmakers, Schoolhouse Museum and Warren Island State Park. A few quick clicks is all it takes to build your ideal Islesboro vacation on Expedia.
Top Islesboro Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Harborline Hotel
Price was CA $2,173, price is now CA $1,721 per person
CA $1,721
per person
Jul 31 - Aug 5
found 14 hours ago
Roundtrip flight included
Montreal (YMQ) to Rockland (RKD)
7.6/10 Good! (266 reviews)
There was little to no hot water during our stay. The front desk staff assured us a manager would be in touch, but that never happened.
Reviewed on Jun 28, 2026
Islesboro Hotel Deals
Island log home in Maine with ocean views
Islesboro ME
10/10 Exceptional! (89 reviews)
"The cabin was perfect for us, especially the location. Host was very accommodating and available if we had any questions. Will definitely stay here again!"
Reviewed on Jun 16, 2026
Secluded And Rustic Island Cabin On The Bold And Rocky Penobscot Bay Coast...
Islesboro ME
10/10 Exceptional! (18 reviews)
Great Spot
"Excellent host! Great connections on the island for everything. Great information on Ferry status, etc. Cabin is truly rustic, spartan appointments as described. Great location and view west with good weather. Bring your goodies, luxuries from the mainland. Lobsters are available tho!"
Reviewed on Nov 29, 2023
Colonial Gables Oceanfront Village
7 Eagle Avenue Belfast ME
Fully refundableReserve now, pay when you stay
The price is CA $210 per night from Jul 5 to Jul 6
CA $210
CA $229 total
Jul 5 - Jul 6
includes taxes & fees
9.6/10 Exceptional! (1,006 reviews)
"We had a great stay. the room was really clean!"
Reviewed on Jun 28, 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Stay near popular Islesboro attractions
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
